(4-fluoro-2-mercaptophenyl)acetic acid | 77795-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: (4-fluoro-2-mercaptophenyl)acetic acid
• 英文别名: 2-(4-Fluoro-2-sulfanylphenyl)acetic acid
• CAS: 77795-39-2
• 化学式: C₈H₇FO₂S
• 分子量: 186.207
• InChiKey: IVTRKWAJPRFLQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-fluoro-2-mercaptophenyl)acetic acid 在 sodium hydroxide 、 sodium tetrahydroborate 、 PPA 、 铁粉 、 potassium carbonate 、 potassium iodide 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 20.0h， 生成 3-fluoro-8-iodo-10,11-dihydrodibenzothiepin-10-ol
  参考文献：
  名称：

  Fluorinated tricyclic neuroleptics with prolonged action: 3-Fluoro-8-halogeno derivatives of 10-piperazino-10,11-dihydrodibenzo[b,f]thiepins

  摘要：

  (4-氟-2-碘苯基)乙酸与4-氟和4-溴噻吩酚反应，得到酸IIIa和IIIc，它们被环化成3-氟-8-卤代二苯并[ b,f ]噻吩-10(11H)-酮IVa和IVc。通过中间体VIac和VIIac得到了标题化合物Ia和IIc。(4-氟-2-巯基苯基)乙酸或6-氟苯并[ b ]噻吩-2(3H)-酮与4-氯硝基苯反应，得到硝基酸IIIe，再还原成氨基酸IIIf。环化反应得到氨基酮IVf，转化为碘代酮IVd。通过中间体VId和VIId得到最终产物IId。化合物Ia和IIcd具有强烈的中枢抑制和僵硬作用；效果的延长仅与中枢抑制成分有关。

  DOI：

  10.1135/cccc19811788
• 作为产物：
  描述：

  2-[2-[[2-(Carboxymethyl)-5-fluorophenyl]disulfanyl]-4-fluorophenyl]acetic acid 生成 (4-fluoro-2-mercaptophenyl)acetic acid
  参考文献：
  名称：

  SINDELAR, K.;PROTIVA, M.

  摘要：

  DOI：

文献信息

• Fluorinated tricyclic neuroleptics with prolonged action: 3-Fluoro-8-trifluoromethyl derivatives of 10-(4-methylpiperazino)- and 10-[4-(2-hydroxyethyl)piperazino]-10,11-dihydrodibenzo-[b,f]thiepin
  作者：Karel Šindelář、Miroslav Ryska、Jiří Holubek、Emil Svátek、Jiřina Metyšová、Jiří Protiva、Miroslav Protiva

  DOI：10.1135/cccc19810118

  日期：——

  A reaction of (4-fluoro-2-iodophenyl)acetic acid with 4-(trifluoromethyl)thiophenol gave the acid VIII which was cyclized with the reagent consisting from methanesulphonic acid and phosphorus pentoxide and afforded the methanesulphonic enol ester XIX. The alkaline hydrolysis resulted in 3-fluoro-8-trifluoromethyldibenzo[b,f]thiepin-10(11H)-one (XVI) which was transformed via the alcohol XXIV to the chloro derivative XXV. Substitution reactions with 1-methylpiperazine and 1-(2-hydroxyethyl)piperazine resulted in the title compounds IV and V. These products are very potent cataleptic neuroleptic agents with a prolongation of duration of the effects comparable to that of isofloxythepin and tefluthixol. A series of further synthetic experiments aimed at alternative syntheses of the acid VIII and the ketone XVI; their results were mostly not of use for preparative purpose but they led to isolation and characterization of a series of interesting heterocyclic products (XVII, XVIII, XXII, XXIII, XXIX-XXXI, XXXVI-XXXIX).

  (4-氟-2-碘苯基)乙酸与4-(三氟甲基)硫代苯酚反应，生成酸VIII，然后与由甲磺酸和五氧化二磷组成的试剂环化，生成甲磺酸烯基酯XIX。碱性水解产生3-氟-8-三氟甲基二苯并[bf]噻吩-10(11H)-酮(XVI)，通过醇XXIV转化为氯衍生物XXV。与1-甲基哌嗪和1-(2-羟乙基)哌嗪的取代反应产生IV和V。这些产物是非常有效的猫病性镇静剂，其效果持续时间延长，与异氟沙替平和替氟西乐相当。一系列进一步的合成实验旨在寻找酸VIII和酮XVI的替代合成方法；它们的结果大多数并没有用于制备目的，但导致了一系列有趣的杂环产物(XVII、XVIII、XXII、XXIII、XXIX-XXXI、XXXVI-XXXIX)的分离和表征。
• SINDELAR K.; RYSKA M.; HOLUBEK J.; SVATEK E.; METYSOVA J.; PROTIVA J.; PR+, COLLECT. CZECH. CHEM. COMMUN., 1981, 46, NO 1, 118-140
  作者：SINDELAR K.、 RYSKA M.、 HOLUBEK J.、 SVATEK E.、 METYSOVA J.、 PROTIVA J.、 PR+

  DOI：——

  日期：——
• PROTIVA, M.;SINDELAR, K.;METYSOVA, J.;HOLUBEK, J.;RYSKA, M.;SVATEK, E.;SE+, COLLECT. CZECH. CHEM. COMMUN., 1981, 46, N 8, 1788-1799
  作者：PROTIVA, M.、SINDELAR, K.、METYSOVA, J.、HOLUBEK, J.、RYSKA, M.、SVATEK, E.、SE+

  DOI：——

  日期：——
• SINDELAR, K.;PROTIVA, M.
  作者：SINDELAR, K.、PROTIVA, M.

  DOI：——

  日期：——
• Fluorinated tricyclic neuroleptics with prolonged action: 3-Fluoro-8-halogeno derivatives of 10-piperazino-10,11-dihydrodibenzo[b,f]thiepins
  作者：Miroslav Protiva、Karel Šindelář、Jiřina Metyšová、Jiří Holubek、Miroslav Ryska、Emil Svátek、Zdeněk Šedivý、Josef Pomykáček

  DOI：10.1135/cccc19811788

  日期：——

  Reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-fluoro and 4-bromothiophenol gave the acids IIIa and IIIc which were cyclized to 3-fluoro-8-halogenodibenzo[b,f]thiepin-10(11H)-ones IVa and IVc. The title compounds Ia and IIc were obtained via the intermediates VIac and VIIac. Reactions of (4-fluoro-2-mercaptophenyl)acetic acid or 6-fluorobenzo[b]thiophen-2(3H)-one with 4-chloronitrobenzene afforded the nitro acid IIIe which was reduced to the amino acid IIIf. Cyclization gave the amino ketone IVf which was transformed to the iodo ketone IVd. Proceeding via the intermediates VId and VIId led to the final product IId. Compounds Ia and IIcd have strong central depressant and cataleptic activity; prolongation of the effect is connected merely with the central depressant component of the action.

  (4-氟-2-碘苯基)乙酸与4-氟和4-溴噻吩酚反应，得到酸IIIa和IIIc，它们被环化成3-氟-8-卤代二苯并[ b,f ]噻吩-10(11H)-酮IVa和IVc。通过中间体VIac和VIIac得到了标题化合物Ia和IIc。(4-氟-2-巯基苯基)乙酸或6-氟苯并[ b ]噻吩-2(3H)-酮与4-氯硝基苯反应，得到硝基酸IIIe，再还原成氨基酸IIIf。环化反应得到氨基酮IVf，转化为碘代酮IVd。通过中间体VId和VIId得到最终产物IId。化合物Ia和IIcd具有强烈的中枢抑制和僵硬作用；效果的延长仅与中枢抑制成分有关。